48 Hours in Pawling


a relaxing weekend away

If you’re craving a relaxing weekend away, our humble town of Pawling is one of the Hudson Valley’s best-kept secrets. "While the village bustles, the rest of the town feels quiet, with more than 400 acres of parkland and 1,100 acres of protected land," says the New York Times.  Pawling is close enough to New York for an easy escape, but far enough away to feel like a different world.

Friday Afternoon: Settle In


May we suggest starting your weekend by turning off your phone and taking a nap? Our beds and pillows get rave reviews.


For dinner, make a reservation at McKinney & Doyle, a longtime Pawling staple that prides itself on “serious cuisine in a not-so-serious atmosphere.” Sit at the bar for a cocktail beforehand and count how many locals greet each other by name around you. Then, settle into a cozy booth to enjoy favorites like avocado egg rolls, Coulette steak, and mushroom carnitas rigatoni. 


On your (very short) walk home, grab a delicious cone of hand-crafted local ice cream at Normby Creamery. 

Saturday Morning: Shopping and Fresh Air


Start with a visit to family-owned Sunflour Bakery, which roasts its own coffee and offers delicious pastries along with breakfast sandwiches and more.


In the summer months, the Pawling Farmers Market sets up on the Village Green across from Station Inn, offering entertainment like magicians and balloon art for kids, live music under the gazebo, and plenty of artisans and farmers selling their wares.


In a shopping mood? Check out gifts at Good Tidings and T&M Home, art at the Live 4 Art and LAND galleries, books and antiques at The Book Cove and Pawling Antiques, clothes and jewelry at NicolJoe, artisanal olive oil and vinegar at The Blue Olive, and well-curated secondhand goods at Ruby’s Nest.  

Saturday Afternoon and Evening: Good Food and Nature


For lunch, stop by the cozy O’Connors Public House for a hamburger or fish and chips to fuel up for the day ahead or grab a to-go Italian sandwich at Food Network-famous Vinny’s Deli.


Next, nature awaits! We love Cats Rock trail, a portion of the Appalachian Trail with especially impressive foliage views in fall. It’s short enough to do with kids or those who don’t consider themselves hikers, but has enough of an incline at the end to get your heart racing. Spread out on the rocks at the top of the peak with a picnic and enjoy the birds-eye view of Pawling. 


For dinner, make your way to Cornerstone Pawling for wood-fired pizzas and farm-to-table entrees with an Italian flair. 

Sunday: Reset for the Week


Nothing says day of rest like the Sunday morning yin yoga class at Pawling Yoga & Wellness. The studio, currently situated at Akin Free Library on Quaker Hill, is a serene gem, with friendly instructors and a warm community vibe.


Afterwards, make your way to La Guadalupana Mini-Mart for a breakfast burrito or sit down at cozy Main Street Cafe for huevos rancheros or other Mexican and Guatemalan favorites. 


Before heading back home, delight in a truly unique museum collection at the Akin Free Library (open weekends from May - October), which boasts natural history specimens and a “cabinet of curiosities" full of everything from preserved snake eggs to tiles from ancient ruins to a jar full of spoons recovered from the stomach of a psychiatric patient. We told you Pawling has everything.

5 Favorite Hiking Trails Near Pawling, NY

September 25, 2026
We know many of our guests are avid hikers, whether they're completing the whole Appalachian Trail or just looking for a casual Sunday saunter. Here are five beautiful trails just a stone's throw from Station Inn. 5 Favorite Hikes Near Pawling, NY Appalachian Trail from the AT Train Stop (Great Swamp Boardwalk & Corbin Hill) Easy to Moderate | 3–12 miles depending on route Right off the Appalachian Trail stop on the Metro-North Harlem Line, this trail begins with a magical 1,600 foot boardwalk spanning the Great Swamp. Walk among the reeds then find yourself back in the trees; follow the trail long enough and it’ll lead across West Dover Road up to Cat Rocks. Cat Rocks via the Appalachian Trail Moderate | ~1.8 miles (short version) or 7.2 miles out-and-back from the AT train stop Right in the parking area for this hike, you'll meet a local celebrity—the Dover Oak, the largest tree on the AT. Then, embark on a challenging but short climb with a satisfying payoff. At the top, spread out on Cat Rocks with a picnic and enjoy gorgeous views of surrounding mountains, farms, and the town of Pawling. Pawling Nature Reserve Easy to Moderate | Multiple trails totaling ~12 miles The multiple trails in this 1,060-acre area will bring you through a gorge rimmed by hemlocks, swamps, overgrown fields, meadows, fern glens, and forested uplands. The tree-species guessing game along the trail is a great distraction for curious kids, as are the frogs and salamanders bubbling in spring’s vernal pools. Dover Stone Church Preserve Easy | ~1 mile to the cave, 4+ miles of additional trails This enchanting trail in nearby Dover leads to a cathedral-like rock formation christened the Dover Stone Church, a fissure in metamorphic rock through which a brook flows, forming ledges and cascades which descend into a pool below. Kids and adults alike will love darting across the rocks and exploring the cavern. Kent Falls State Park Easy to Moderate | ~0.8–1.1 miles Just across the Connecticut line and well worth the quick drive, Kent Falls offers a chance to wander across an old-fashioned covered bridge and feel the mist on your face as water cascades 250 feet down to the Housatonic River. Check out the charming village of Kent after the hike for lunch and shopping. Ascend the steps to see waterfall after waterfall, or head into the woods for a quieter walk.
Living room with dark wood furniture, blue chairs, and a large window.

Chapman House Writing Residency: Sunday November 15 - Friday November 20, 2026

September 30, 2025
This November, we are excited to offer our second annual no-cost writing residency to four writers at the Chapman House, a property of Station Inn Pawling, hosted in partnership with the Pawling Library. The dates for this year’s residency are Sunday November 15 – Friday November 20. This residency is open to emerging writers of fiction, memoir, poetry, and nonfiction. We define "emerging" to include writers who have not yet published a book-length project and do not have one forthcoming in the next year. The Chapman House has four beautiful suites set in the heart of the charming Village of Pawling. We hope the time away from routine and responsibility will provide fertile ground for creative inspiration. Write, hike on the nearby Appalachian trail, connect with the other writers, soak up small-town life, or just take time to let your brain settle and ideas germinate. We are excited to partner with the Pawling Library to host a public reading and reception featuring the residents on Thursday, November 19. The library will also provide a dedicated workspace for the residents to use for the week.